Dicyclohexylcarbodiimide → HCID 67606929, compound

HRID 1619575Notes

Reaction equation

HRID 1619575 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:53]12[CH2:60][CH2:59][CH:56]([CH2:57][CH2:58]1)[C@@H:55](O)[CH2:54]2>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([O:19][C@@H:55]2[CH:56]3[CH2:59][CH2:60][N:53]([CH2:58][CH2:57]3)[CH2:54]2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine

Product 1

HCID 67606929HCID 67606929, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-3-(4-(benzyloxy)phenyl)-2-(tert-butoxycarbonyl-amino)propanoic acid (500 mg, 1.35 mmol), DCC (333 mg, 1.61 mmol) and HOBT (247 mg, 1.61 mmol) in dry THF (10 ml) was stirred at RT under nitrogen atmosphere for 1 hour. (R)-quinuclidin-3-ol (205 mg, 1.61 mmol) was added, and the reaction was stirred for 16 hours. The solvent was evaporated, and the residue was portioned between saturated NaHCO3 and EtOAc. The organic phase was washed with brine, dried over Na2SO4 filtered and evaporated to dryness. The residue was triturated with Et2O (30 ml), and the insoluble material was removed by filtration. The solution was evaporated to obtain (S)—((R)-quinuclidin-3-yl) 3-(4-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)-propanoate (590 mg, 91% yield).

Workup

  1. stirringthe reaction was stirred for 16 hours
  2. customThe solvent was evaporated
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was triturated with Et2O (30 ml)
  8. customthe insoluble material was removed by filtration
  9. customThe solution was evaporated

Sources & evidence

ORD record
ord-2209fe356b39437aaec177b5c006e534
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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